Sulfonate surfactants and methods of preparation and use   

FIELD OF THE INVENTION

The invention relates to new sulfonate surfactants, compositions of new sulfonate surfactants, and methods of preparation and use of the surfactants.

BACKGROUND OF THE INVENTION

Anionic surfactants are well known and have been used in a variety of applications, including for instance in cleaners and detergents. Common anionic surfactants, such as linear alkylbenzene sulfonate (LAS) and alcohol sulfates (for example sodium lauryl sulfate), however, have poor solubilities in cold water or hard water, and in caustic. So too do alkyl glycerol sulfonate (AGS) surfactants prepared from, for example, epichlorohydrin, a linear alkyl alcohol, and sodium sulfite. This lack of solubility limits the formulation options and the performance of these surfactants.

Providing anionic surfactants with an improved spectrum of properties, such as high solubility in cold, hard, caustic and ionic water while maintaining high surface activity remains a challenge for anionic surfactants.

SUMMARY

In one aspect, the invention provides novel anionic sulfonate surfactants. The anionic surfactants are compounds of formula I, or mixtures of two or more thereof:

wherein R, R1, R2, R3, R4, R5, and R6 are as defined below.

In another aspect, the invention provides a formulation containing one or more anionic surfactants of formula I.

In a further aspect, the invention provides cleaning compositions comprising a surfactant of formula I.

In a still further aspect, the invention provides a process for making an anionic surfactant of formula I or mixtures of two or more thereof.

FIG. 1 is a graph showing examples of surfactant compositions that can be obtained through the processes of the invention.

FIG. 2 is a graph showing surface tension results for anionic surfactants of the invention compared with a non-inventive surfactant.

FIG. 3 is a graph showing dynamic surface tension results for anionic surfactants of the invention compared with a non-inventive surfactant.

FIG. 4 is a graph showing Ross-Miles foaming test results for anionic sufactants of the invention compared with a non-inventive surfactant.

FIG. 5 is a graph comparing cleaning efficiency of an inventive formulation with a comparative formulation.

DETAILED DESCRIPTION

As noted above, in one aspect, the invention provides novel anionic surfactants. An anionic surfactant of the invention contains two sulfonate groups, or one sulfonate and one hydroxy group, on a branched alkyl ether backbone. The anionic surfactants exhibit an improved spectrum of properties relative to other known disulfonate and hydroxy sulfonate (e.g., AGS) surfactants, allowing them to be used in a wide variety of applications. For instance, surfactants of the invention are highly soluble in water, have high tolerance to hard water, electrolytes, and caustic solutions and, when used in cleaning compositions, provide excellent performance in the removal of greasy soils. In addition, as demonstrated by the examples, surfactants of the invention exhibit highly favorable aquatic toxicity.

The anionic surfactants of the invention are compounds of formula I:

wherein R is linear or branched C2-C22 alkyl;

R1, R2, and R3 are independently H or linear or branched C1-C18 alkyl;

R4 is H, CH2SO3−M+, or CH2OH;

R5 is OH, SO3−M+, or a group of the formula:

R6 is H, CH2SO3−M+, or CH2OH; and

M+ is H+ or a monovalent or divalent cation, such as sodium, potassium, ammonium, calcium, magnesium, or alkylated ammonium,

wherein one of R4 and R6 is H and wherein one or two of R4, R5, or R6 contains SO3−M+.

The processes described below for preparing the surfactants of the invention may result in the formation of mixtures of compounds of formula I. Although the individual compounds of formula I may be isolated from the mixture, this step is not necessary, and indeed it is sometimes preferred that the surfactant be used in the form of the mixture. Thus, surfactants that are mixtures of compounds of formula I are contemplated and are within the scope of the invention.

Preferred surfactants of formula I include compounds of formula I-1 (or mixtures thereof), which are compounds of formula I wherein R is linear C2-C22 alkyl. Further preferably, R is linear or branched, more preferably linear, C4-C16 alkyl.

Preferred compounds of formulae I and I-1 include compounds of formula I-2, which are compounds of formula I or I-1 wherein R1 is H.

Preferred compounds of formulae I, I-1, and I-2 include compounds of formula I-3, which are compounds of formula I, I-1 or I-2 wherein R2 is H.

Preferred compounds of formulae I, I-1, I-2, and I-3 include compounds of formula I-4, which are compounds of formula I, I-1, I-2 or I-3 wherein R3 is H.

Preferred compounds of formulae I, I-1, I-2, I-3, and I-4 include compounds of formula I-5, which are compounds of formula I, I-1, I-2, I-3, or I-4 wherein R4 is CH2SO3−M+ or CH2OH. In one embodiment, R4 is preferably CH2SO3−M+. In another embodiment, R4 is preferably CH2OH.

Preferred compounds of formulae I, I-1, I-2, I-3, I-4, and I-5 include compounds of formula I-6, which are compounds of formula I, I-1, I-2, I-3, I-4, or I-5 wherein R5 is OH or SO3−M+. In one embodiment, R5 is preferably SO3−M+. In another embodiment, R5 is preferably OH.

Preferred compounds of formulae I, I-1, I-2, I-3, I-4, I-5, and I-6 include compounds of formula I-7, which are compounds of formula I, I-1, I-2, I-3, I-4, I-5, or I-6 wherein R6 is H.

Preferred compounds of formulae I, I-1, I-2, I-3, I-4, I-5, I-6, and I-7 include compounds of formula I-8, which are compounds of formula I, I-1, I-2, I-3, I-4, I-5, I-6, or I-7 wherein M+ is H+ or a monovalent cation. Further preferably, M+ is H+, Na+, K+, ammonium or alkylated ammonium. Particularly preferred is Na+.

Preferred compounds of formula I further include compounds of formula II:

wherein R is linear or branched C2-C22 alkyl;

R1, R2, and R3 are independently H or linear or branched C1-C18 alkyl;

R4 is CH2SO3−M+ or CH2OH;

R5 is OH or SO3−M+; and

M+ is H+, or a monovalent or divalent cation, wherein one or both of R4 and R5 contains SO3−M+.

Preferred compounds of formula II include compounds of formula II-1, which are compounds of formula II wherein R is linear C2-C22 alkyl. Further preferably, R is linear or branched, more preferably linear, C4-C16 alkyl.

Preferred compounds of formulae II and II-1 include compounds of formula II-2, which are compounds of formula II or II-1 wherein R1, R2, and R3 are each H.

Preferred compounds of formulae II, II-1, and II-2 include compounds of formula II-3, which are compounds of formula II, II-1, or II-2 wherein R4 is CH2SO3−M+ and R5 is OH.

Preferred compounds of formulae II, II-1, and II-2 include compounds of formula II-4, which are compounds of formula II, II-1, or II-2 wherein R4 is CH2SO3−M+ and R5 is SO3−M+.

Preferred compounds of formulae II, II-1, II-2, II-3, and II-4 include compounds of formula II-5, which are compounds of formula III, II-1, II-2, II-3, or II-4 wherein M+ is H+ or a monovalent cation. Further preferably, M+ is H+, Na+, K+, ammonium or alkylated ammonium. Particularly preferred is Na+.

In some embodiments of the invention, the compounds of formula I are of the formula III:

wherein R is linear or branched C2-C22 alkyl;

R1, R2, and R3 are independently H or linear or branched C1-C18 alkyl;

R5 is OH or SO3−M+;

R6 is CH2SO3−M+ or CH2OH; and

M+ is H+, or a monovalent or divalent cation, wherein one or both of R5 and R6 contains SO3−M+.

Preferred compounds of formula III include compounds of formula III-1, which are compounds of formula III wherein R is linear C2-C22 alkyl. Further preferably, R is linear or branched, more preferably linear, C4-C16 alkyl.

Preferred compounds of formulae III and III-1 include compounds of formula III-2, which are compounds of formula III or III-1 wherein R1, R2, and R3 are each H.

Preferred compounds of formulae III, III-1, and III-2 include compounds of formula III-3, which are compounds of formula III, III-1, or III-2 wherein R5 is OH and R6 is CH2SO3−M+.

Preferred compounds of formulae III, III-1, and III-2 include compounds of formula III-4, which are compounds of formula III, III-1, or III-2 wherein R5 is SO3−M+ and R6 is CH2OH.

Preferred compounds of formulae III, III-1, and III-2 include compounds of formula III-5, which are compounds of formula III, III-1, or III-2 wherein R5 is SO3−M+ and R6 is CH2SO3−M+.

Preferred compounds of formulae III, III-1, III-2, III-3, III-4, and III-5 include compounds of formula III-6, which are compounds of formula I III, III-1, III-2, III-3, III-4, or III-5 wherein M+ is H+ or a monovalent cation. Further preferably, M+ is H+, Na+, K+, ammonium or alkylated ammonium. Particularly preferred is Na+.

Preferred anionic surfactants of the invention include the compounds shown in Table 1:

TABLE 1 Name Structure Sodium 2-hexan-2- yloxypropane-1,3- disulfonate Sodium 2-hexan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-octan-2- yloxypropane-1,3- disulfonate Sodium 2-octan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-decan-2- yloxypropane-1,3- disulfonate Sodium 2-decan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-dodecan-2- yloxypropane-1,3- disulfonate Sodium 2-dodecan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-tetradecan-2- yloxypropane-1,3- disulfonate Sodium 2-tetradecan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-hexadecan-2- yloxypropane-1,3- disulfonate Sodium 2-hexadecan-2- yloxy-3- hydroxypropane-1- disulfonate Sodium 2-octadecan-2- yloxypropane-1,3- disulfonate Sodium 2-octadecan-2- yloxy-3- hydroxypropane-1- disulfonate

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